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Hypatulone A, a Homoadamantane-Type Acylphloroglucinol with an Intricately Caged Core from Hypericum patulum
journal contribution
posted on 2018-12-10, 11:29 authored by Yang-Yang Liu, Zhen Ao, Gui-Min Xue, Xiao-Bing Wang, Jian-Guang Luo, Ling-Yi KongHypatulone
A (1), an acylphloroglucinol possessing an unprecedented
homoadamantane architecture based on a tricyclo-[4.3.1.13,8]-undecane core and a unique 5/5/7/6/6 pentacyclic ring system, together
with its biogenetic precursor hyperbeanol B (2), was
isolated from Hypericum patulum. The
structure of 1 was elucidated by extensive spectroscopic
analysis and electronic circular dichroism calculation. Its plausible
biosynthetic pathway via Wagner–Meerwein rearrangement was
proposed. 1 exhibited nitric oxide inhibitory effect
on LPS-induced RAW264.7 cell line (IC50 18.8 ± 1.75
μM).
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ICpentacyclicHypericum patulum Hypatulone18.8coreIntricately Caged CoreHomoadamantane-Type Acylphloroglucinolhomoadamantane architecturerearrangementacylphloroglucinolspectroscopic analysisbiosynthetic pathway1.75nitric oxideundecanebiogenetic precursor hyperbeanol BWagnertricycloHypericum patulumdichroism calculationLPS-induced RAW 264.7 cell line
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